Custom sail cruises in Point Loma provide a front-row seat

Passenger Stephen Gallogly reclines on the boat to savor the scenery.

The weather on Monday, Feb. 25 along the harbor off Shelter Island was perfect for the first time in many winter weeks. The wind was light and breezy, the sun was warm, the waves were calm, Karl the baby gray whale was making an appearance, and the five guests aboard Sail San Diego’s sunset cruise were soaking up the whole adventure.

Sail San Diego invited PB Monthly along to experience one of their intimate voyages.

Passenger Anne Middaugh relaxes at the bow of the boat to enjoy the ocean breeze.
Passenger Anne Middaugh relaxes at the bow of the boat to enjoy the ocean breeze.
( Savanah Duffy )

At the moment, the company’s office is getting a makeover, said marketing director Chaluim (Cal) Muir, who became the first deckhand at age 14 when he started cleaning boats for owners Tim and Michele Hanley. A lounge area is being added where guests can complete the “nitty-gritty” part of sailing, as Cal put it, such as paperwork.

Nitty-gritty aside, it’s clear that Sail San Diego is all about hospitality and making sure passengers enjoy themselves. Cal and Captain Theo Niekras, who sailed the ship the day we went out, were incredibly courteous, helpful, personable and often times hilarious.

While chatting with Cal, I learned that the mammals seen during whale-watching season are gray whales migrating from Alaska south to Baja California, Mexico, where they enter lagoons to give birth and mate. They’re spotted in San Diego because they keep close to the shore and calmer waters.

I asked whether I’d see any whales on the three-hour excursion. Captain Theo, who had joined us, piped up enthusiastically: “One snot on me yesterday!”

Two sea lions cause a ruckus before initiating a squabble.
Two sea lions cause a ruckus before initiating a squabble.
( Savanah Duffy )

While that might not sound terribly appealing, Theo was clearly excited about the encounter — and had proudly showed his whale snot-soaked glasses to the guests on board.

Theo insisted that the whale in question is the same baby whale who showed up last year and became his friend, and whom Theo refers to as “Karl.”

“Karl with a ‘K,’” he emphasized.

San Diegan Cody Castro watches the sun set.
(Savanah Duffy)

Sitting on deck before we set sail, I got a little worried about sunburn, and the wind was chillier than I expected, but I didn’t need to be concerned. Cal announced that, in addition to sunscreen, there were blankets, jackets and even Snuggies in the cabin, along with sunglasses, snacks, beer, white wine and non-alcoholic drinks.

They even had a tub of Red Vines (licorice) — a true weakness of mine.

After an informative talk, Cal handed us off to Captain Theo, exited the boat, and we were off! From start to finish, the trip was relaxing and entirely beautiful, and heightened by the enjoyable company onboard.

Cody Castro, Chris Odom, Captain Theo
(Savanah Duffy)

As the breeze carried us slowly through the deep blue waters and further from the docks, Theo speculated that perhaps we’d see his good friend Karl during the trip. “We’ve got a special something going on between us,” he confided.

The further we sailed into the harbor, the more wildlife we saw. We watched as pelicans skimmed the water, and seals swam alongside our boat, splashing and catching fish. Theo provided entertaining commentary throughout the journey.

Captain Theo (left) and passenger Stephen Gallogly share a laugh and steer the boat together.
(Savanah Duffy)

One of the guests, Stephen Gallogly, said he’s done some sailing of his own, and every now and then, Theo would ask for Stephen’s help to steer or work the sails. Guest Anne Middaugh, who had a smile on her face from the moment she boarded, climbed to the boat’s bow to relax, watch for whales, and enjoy the view and cool winds.

A splash of water alerted Theo to Karl’s arrival, and as the boat sailed closer to the whale, we all sat up straight and craned our necks to get a glimpse of him breaching the water and gracing us with his presence.

A gray whale breaches the water and blows air through his blowhole.
A gray whale breaches the water and blows air through his blowhole.
( Savanah Duffy )

We continued out toward open waters, past where the U.S. Navy trains dolphins, past a floating dock where sea lions lounged lazily atop one another, and around the tip of the Point Loma peninsula.

Once out in open waters, we kicked back, took photos, joked around and enjoyed the complimentary white wine. I, for one, enjoyed quite a few Red Vines.

Watching the sun set from the ocean was a truly stunning experience.

By the time we returned to the dock, the sun was low and the winds grew colder. We said a big thank you to Captain Theo, sent good vibes out to Karl, and headed home to enjoy the rest of a cool San Diego evening.


About Sail San Diego

• Sail San Diego has been in operation since 1988, offering sailing lessons and custom tours to small groups — specializing in whale-watching excursions, typically from January to April. (If you don’t see any whales on your trip, let them know and you can go out again on another day for free!)

• Location: 2646 Shelter Island Drive

• Hours: 8 a.m. to 6 p.m. daily

• Contact: (619) 297-7426,

• Cost: $95 per person (standard 3 hours); private tours for 6 people $550, plus $95 extra per person, up to 12

• Captains: U.S. Coast Guard-certified

• Boats: 40-foot Catalina sailing vessels, chosen for comfort and safety